DE1692035C3 - Arzneimittel mit bronchodilatorischer Wirkung - Google Patents

Arzneimittel mit bronchodilatorischer Wirkung

Info

Publication number: DE1692035C3
Authority: DE; Germany
Prior art keywords: hydroxy; drug; aerosol; medicines; inhalation
Prior art date: 1967-02-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

DE19681692035

Other languages

German (de)

English (en)

Other versions

DE1692035B2 (de

DE1692035A1 (de

Inventor

Milton Rosemont Lapidus

Marvin Emmanuel Havertown Rosenthale

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth LLC

Original Assignee

American Home Products Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1967-02-20

Filing date

1968-02-19

Publication date

1975-06-19

1968-02-19 Application filed by American Home Products Corp filed Critical American Home Products Corp

1972-05-04 Publication of DE1692035A1 publication Critical patent/DE1692035A1/de

1974-10-24 Publication of DE1692035B2 publication Critical patent/DE1692035B2/de

1975-06-19 Application granted granted Critical

1975-06-19 Publication of DE1692035C3 publication Critical patent/DE1692035C3/de

Status Expired legal-status Critical Current

Links

239000003814 drug Substances 0.000 title claims description 22
229940079593 drug Drugs 0.000 title claims description 18
230000000694 effects Effects 0.000 title claims description 9
229940124630 bronchodilator Drugs 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims 1
239000000443 aerosol Substances 0.000 description 15
239000000243 solution Substances 0.000 description 12
-1 C 1 -C 6 -Alk ^ l Chemical class 0.000 description 10
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
241000700198 Cavia Species 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000003380 propellant Substances 0.000 description 6
206010010904 Convulsion Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
230000036461 convulsion Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
239000007921 spray Substances 0.000 description 5
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
229960001340 histamine Drugs 0.000 description 4
238000000034 method Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000029058 respiratory gaseous exchange Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
239000004338 Dichlorodifluoromethane Substances 0.000 description 3
241001071864 Lethrinus laticaudis Species 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000006184 cosolvent Substances 0.000 description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
238000002156 mixing Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
238000005507 spraying Methods 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000009079 Bronchial Spasm Diseases 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
208000007101 Muscle Cramp Diseases 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
208000005392 Spasm Diseases 0.000 description 2
239000000150 Sympathomimetic Substances 0.000 description 2
229960003556 aminophylline Drugs 0.000 description 2
FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000168 bronchodilator agent Substances 0.000 description 2
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 2
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 2
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
229960002179 ephedrine Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000002664 inhalation therapy Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 2
WGCXTGBZBFBQPP-UHFFFAOYSA-N methyl 7-[3-hydroxy-2-(3-hydroxyoct-1-enyl)-5-oxocyclopentyl]hept-5-enoate Chemical compound CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(=O)OC WGCXTGBZBFBQPP-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
238000011282 treatment Methods 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
229930182837 (R)-adrenaline Natural products 0.000 description 1
RXYPXQSKLGGKOL-UHFFFAOYSA-O 1,4-dimethylpiperazin-1-ium Chemical compound CN1CC[NH+](C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-O 0.000 description 1
AXWLKJWVMMAXBD-UHFFFAOYSA-N 1-butylpiperidine Chemical compound CCCCN1CCCCC1 AXWLKJWVMMAXBD-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-O 1-methylpiperidin-1-ium Chemical compound C[NH+]1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-O 0.000 description 1
YQOPNAOQGQSUHF-UHFFFAOYSA-N 1-propan-2-ylpyrrolidine Chemical compound CC(C)N1CCCC1 YQOPNAOQGQSUHF-UHFFFAOYSA-N 0.000 description 1
NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-O 4-ethylmorpholin-4-ium Chemical compound CC[NH+]1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-O 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
206010053155 Epigastric discomfort Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
241001494479 Pecora Species 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
206010036790 Productive cough Diseases 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
206010041277 Sodium retention Diseases 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
PAFZNILMFXTMIY-UHFFFAOYSA-O cyclohexylammonium Chemical compound [NH3+]C1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-O 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
229960005139 epinephrine Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012634 fragment Substances 0.000 description 1
210000004392 genitalia Anatomy 0.000 description 1
GLUUGHFHXGJENI-UHFFFAOYSA-O hydron piperazine Chemical compound [H+].C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-O 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
201000001421 hyperglycemia Diseases 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940039009 isoproterenol Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
238000002663 nebulization Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
229940127230 sympathomimetic drug Drugs 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical compound OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1
238000010792 warming Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0078—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a nebulizer such as a jet nebulizer, ultrasonic nebulizer, e.g. in the form of aqueous drug solutions or dispersions
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dispersion Chemistry (AREA)
Otolaryngology (AREA)
Pulmonology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

DE19681692035 1967-02-20 1968-02-19 Arzneimittel mit bronchodilatorischer Wirkung Expired DE1692035C3 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US61707267A	1967-02-20	1967-02-20

Publications (3)

Publication Number	Publication Date
DE1692035A1 DE1692035A1 (de)	1972-05-04
DE1692035B2 DE1692035B2 (de)	1974-10-24
DE1692035C3 true DE1692035C3 (de)	1975-06-19

Family

ID=24472128

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19681692035 Expired DE1692035C3 (de)	1967-02-20	1968-02-19	Arzneimittel mit bronchodilatorischer Wirkung

Country Status (4)

Country	Link
BE (1)	BE711025A (ja)
DE (1)	DE1692035C3 (ja)
FR (1)	FR7594M (ja)
GB (1)	GB1213015A (ja)

1968
- 1968-02-13 GB GB7111/68A patent/GB1213015A/en not_active Expired
- 1968-02-19 DE DE19681692035 patent/DE1692035C3/de not_active Expired
- 1968-02-19 FR FR140409A patent/FR7594M/fr not_active Expired
- 1968-02-20 BE BE711025D patent/BE711025A/xx unknown

Also Published As

Publication number	Publication date
DE1692035B2 (de)	1974-10-24
GB1213015A (en)	1970-11-18
BE711025A (ja)	1968-08-20
DE1692035A1 (de)	1972-05-04
FR7594M (ja)	1970-01-12

Legal Events

Date	Code	Title
1975-06-19	C3	Grant after two publication steps (3rd publication)
1977-12-31	E77	Valid patent as to the heymanns-index 1977
1983-04-07	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
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DE3907649C2 (de)	1996-07-11	Arzneimittel, geeignet bei der Bekämpfung von Viren und zur Immunstimulierung
EP0185210B1 (de)	1991-06-12	Verwendung von Dipeptidderivaten für die Herstellung von Arzneimitteln zur Behandlung von an amyotropher Lateralsklerose Erkrankten
DE2360332C2 (de)	1983-12-29	Die Verwendung von 1-Carnitin oder einem 1-Carnitinderivat oder eines Salzes davon bei der Behandlung spezieller Lungenkrankheiten
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EP0474597A2 (de)	1992-03-11	Arachidonsäurestoffwechselhemmende Diphenylverbindungen und ihre Verwendung in pharmazeutischen Zusammensetzungen
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WO1982000293A1 (en)	1982-02-04	Substituted adenosine-3',5'-phosphobenzyl triester derivatives,method for their preparation and medicaments containing such compounds
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DE2749075C2 (ja)	1990-10-25
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EP0192098B1 (de)	1991-08-21	Verwendung des 2-Amino-6-allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepins zur Herstellung eines zur Behandlung der Parkinsonschen Erkrankung bzw. des Parkinsonismus geeigneten Arzneimittels
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